Ammonium formate → HCID 89455849, compound

HRID 1776647Notes

Reaction equation

HRID 1776647 reaction equation
[C:1]([O:5][C:6]([N:8]([C:13]1[CH:34]=[CH:33][C:16]([C:17]([O:19][C:20]([CH3:32])([CH3:31])[C:21]([O:23]CC2C=CC=CC=2)=[O:22])=[O:18])=[CH:15][C:14]=1[O:35][CH2:36][CH:37]1[CH2:39][CH2:38]1)[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]([C:13]1[CH:34]=[CH:33][C:16]([C:17]([O:19][C:20]([CH3:32])([CH3:31])[C:21]([OH:23])=[O:22])=[O:18])=[CH:15][C:14]=1[O:35][CH2:36][CH:37]1[CH2:38][CH2:39]1)[S:9]([CH3:12])(=[O:10])=[O:11])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 89460041HCID 89460041, compound

Product 1

HCID 89455849HCID 89455849, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 1-(benzyloxy)-2-methyl-1-oxopropan-2-yl 4-(N-(tert-butoxycarbonyl)methylsulfonamido)-3-(cyclopropylmethoxy)benzoate (0.5 g, 0.890 mmol) and 10% Pd/C (0.100 g) in MeOH (30 ml), ammonium formate (0.337 g, 5.34 mmol) was added, and the mixture was heated to reflux for 1 hour. After cooling the catalyst was filtered off and the solvent was evaporated; the residue was dissolved in ethyl acetate and washed with 0.5N HCl and brine. The organic phase was dried over Na2SO4, filtered and evaporated to give 2-(4-(N-(tert-butoxycarbonyl)-methylsulfonamido)-3-(cyclopropylmethoxy)benzoyloxy)-2-methylpropanoic acid as a white powder (0.402 g, 0.853 mmol, 96% yield, MS/ESI+ 493.9 [MNa]+).

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 1 hour
  4. temperatureAfter cooling the catalyst
  5. filtrationwas filtered off
  6. customthe solvent was evaporated
  7. dissolutionthe residue was dissolved in ethyl acetate
  8. washwashed with 0.5N HCl and brine
  9. dry with materialThe organic phase was dried over Na2SO4
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-f648f9cff0d24d4292322540d5d303b9
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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